KR20220160478A - Organometallic compounds and organic light emitting diode comprising the same - Google Patents

Abstract

Disclosed is an organic metal compound represented by following chemical formula I which is a metal complex, wherein a structure of additionally applying a fusion ring to a 2-phenylquinoline ligand is combined with central coordination metal. Since the present invention applies the organic metal compound represented by the following chemical formula I as a dopant of a light emitting layer, the present invention can improve color purity as a result of narrowing a half width by applying rigidity to molecules of the organic metal compound.

Description

Organometallic compounds and organic electroluminescent devices containing them {ORGANOMETALLIC COMPOUNDS AND ORGANIC LIGHT EMITTING DIODE COMPRISING THE SAME}

The present invention relates to an organometallic compound, and more particularly, to an organometallic compound having phosphorescent properties and an organic electroluminescent device including the same.

As display devices are applied to various fields, interest is increasing. The technology of an organic light emitting display device including an organic light emitting diode (OLED) as one of such display devices is rapidly developing.

An organic light emitting device is a device that emits energy of the excitons as light after injecting charge into a light emitting layer formed between an anode and a cathode to form excitons (excitons) by pairing electrons and holes. Compared to existing display technologies, organic light emitting diodes can be driven at a lower voltage, consume relatively less power, have excellent color, and can be used in various ways by applying a flexible substrate, and the size of the display device can be freely adjusted. It has the advantage of being able to

Organic light emitting diodes (OLEDs) have excellent viewing angles and contrast ratios compared to liquid crystal displays (LCDs) and do not require a backlight, so they can be lightweight and ultra-thin. An organic light emitting device includes a plurality of organic material layers between a cathode (electron injection electrode) and an anode (hole injection electrode), such as a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron blocking layer, a light emitting layer, and electron transfer. Layers and the like are arranged and formed.

In this organic light emitting device structure, when a voltage is applied between the two electrodes, electrons and holes are injected from the cathode and anode, respectively, and excitons generated in the light emitting layer fall to the ground state and emit light.

Organic materials used in organic light emitting devices can be largely classified into light emitting materials and charge transport materials. The light emitting material is an important factor determining the luminous efficiency of the organic light emitting device, and the light emitting material must have high quantum efficiency, excellent mobility of electrons and holes, and must exist uniformly and stably in the light emitting layer. Light emitting materials are classified into blue, red, green, etc. light emitting materials according to the color light, and are used as a host and dopant to increase color purity and luminous efficiency through energy transfer. .

For organic light emitting devices, there is a continuous demand for development of low driving voltage, high efficiency, and long lifespan. In addition, demand for light emitting materials capable of expressing high-purity colors that can include a wide CIE color coordinate range in OLED display devices is also increasing. The need for light emitting materials to display is even greater.

However, since the visibility decreases as the color purity increases (the CIE color coordinate X value increases), it is difficult to obtain high luminous efficiency with the same internal quantum efficiency. Development of a phosphorescent light emitting material that can be implemented is required.

Accordingly, an object of the present invention is to provide an organometallic compound capable of realizing high color purity and high luminance by improving driving voltage, efficiency, and lifespan, and an organic light emitting device applying the same to an organic light emitting layer.

The objects of the present invention are not limited to the above-mentioned objects, and other objects and advantages of the present invention not mentioned above can be understood by the following description and will be more clearly understood by the examples of the present invention. It will also be readily apparent that the objects and advantages of the present invention may be realized by means of the instrumentalities and combinations thereof set forth in the claims.

In order to solve the above problems, the present invention provides an organometallic compound having a novel structure represented by the following formula (I) and an organic light emitting device using the organic metal compound as a dopant for a light emitting layer.

[화학식 I]

[Formula I]

In the above formula I,

M is a central coordination metal, molybdenum (Mo), tungsten (W), rhenium (Re), ruthenium (Ru), osmium (Os), rhodium (Rh), iridium (Ir), palladium (Pd), platinum (Pt) ) and may be one selected from the group consisting of gold (Au);

R is a fused ring formed by connecting X ₁ and X ₂ ;

R ₁ and R ₂ are each independently hydrogen, deuterium, halogen, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted A substituted C3-C20 cycloalkyl group, a substituted or unsubstituted C1-C20 heteroalkyl group, a substituted or unsubstituted C7-C20 arylalkyl group, a substituted or unsubstituted C1-C20 alkenyl group, a substituted or unsubstituted C3-C20 cycloalkenyl group, substituted or unsubstituted C1-C20 heteroalkenyl group, alkynyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 heteroaryl group, alkoxy It may be one selected from the group consisting of an amino group, a silyl group, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a sulfanyl group, a sulfinyl group, a sulfonyl group, and a phosphino group;

Y is BR ₃ , CR ₃ R ₄ , C=O, CNR ₃ , SiR ₃ R ₄ , NR ₃ , PR ₃ , AsR ₃ , SbR ₃ , P(O)R ₃ , P(S)R ₃ , P( Se)R ₃ , As(O)R ₃ , As(S)R _{3 , As(Se)R 3 ,} Sb(O)R ₃ , Sb(S)R ₃ , Sb(Se)R ₃ , O, S , Se, Te, SO, SO ₂ , SeO, SeO ₂ , TeO and TeO ₂ It may be one selected from the group consisting of;

R ₃ and R ₄ are each independently hydrogen, deuterium, halogen, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted A substituted C3-C20 cycloalkyl group, a substituted or unsubstituted C1-C20 heteroalkyl group, a substituted or unsubstituted C7-C20 arylalkyl group, a substituted or unsubstituted C1-C20 alkenyl group, a substituted or unsubstituted C3-C20 cycloalkenyl group, substituted or unsubstituted C1-C20 heteroalkenyl group, alkynyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 heteroaryl group, alkoxy It may be one selected from the group consisting of an amino group, a silyl group, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a sulfanyl group, a sulfinyl group, a sulfonyl group, and a phosphino group;

X ₃ to X ₆ may each independently be one selected from CR ₅ and N;

Adjacent substituents of X ₃ to X ₆ may be fused to form a ring, and the ring may be a C5-C6 carbon ring or a heterocyclic ring;

X ₇ to X ₁₀ may each independently be one selected from CR ₆ and N;

R ₅ and R ₆ are each independently hydrogen, deuterium, halogen, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted A substituted C3-C20 cycloalkyl group, a substituted or unsubstituted C1-C20 heteroalkyl group, a substituted or unsubstituted C7-C20 arylalkyl group, a substituted or unsubstituted C1-C20 alkenyl group, a substituted or unsubstituted C3-C20 cycloalkenyl group, substituted or unsubstituted C1-C20 heteroalkenyl group, alkynyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 heteroaryl group, alkoxy It may be one selected from the group consisting of an amino group, a silyl group, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a sulfanyl group, a sulfinyl group, a sulfonyl group, and a phosphino group;

는 두 자리 리간드(bidentate ligand)일 수 있고;

can be a bidentate ligand;

m may be an integer of 1, 2 or 3, n may be an integer of 0, 1 or 2, and m+n may be an oxidation number of metal M.

By applying the organometallic compound according to the present invention to the dopant of the light emitting layer of the organic light emitting device, driving voltage, efficiency and lifetime characteristics of the organic light emitting device can be improved.

In addition, by applying the organometallic compound according to the present invention to the dopant of the light emitting layer of the organic light emitting device, the color purity of the organic light emitting device can be improved to realize high color purity and high luminance.

Effects of the present specification are not limited to the effects mentioned above, and other effects not mentioned will be clearly understood by those skilled in the art from the description below.

1 is a cross-sectional view schematically illustrating an organic light emitting device in which an organometallic compound according to an exemplary embodiment of the present invention is applied to a light emitting layer.
2 is a cross-sectional view schematically illustrating an organic light emitting display device to which an organic light emitting device according to an exemplary embodiment of the present invention is applied.
3 and 4 are graphs plotting the emission wavelength and full width at half maximum of an organic light emitting device to which Compound 42 of Example 12 and Compound 145 of Example 22 are applied, respectively, and the vertical axis is the photoluminescence (PL) intensity), and the horizontal axis means wavelength (nm).
5 is a cross-sectional view schematically illustrating an organic light emitting device having a tandem structure including two light emitting units according to an exemplary embodiment of the present invention and including an organometallic compound represented by Chemical Formula I.

The above objects, features and advantages will be described later in detail with reference to the accompanying drawings, and accordingly, those skilled in the art to which the present invention belongs will be able to easily implement the technical spirit of the present invention. In describing the present invention, if it is determined that the detailed description of the known technology related to the present invention may unnecessarily obscure the subject matter of the present invention, the detailed description will be omitted. Hereinafter, preferred embodiments according to the present invention will be described in detail with reference to the accompanying drawings. In the drawings, the same reference numerals are used to indicate the same or similar components.

In describing the present specification, if it is determined that a detailed description of related known technologies may unnecessarily obscure the gist of the present specification, the detailed description will be omitted.

In this specification, when 'includes', 'has', 'consists of', 'arranges', etc. is used for a component, other parts may be added unless 'only' is used. In the case where a component is expressed in the singular, the case including the plural is included unless otherwise explicitly stated.

In interpreting the components in this specification, it is interpreted as including the error range even if there is no separate explicit description.

In this specification, the arrangement of an arbitrary element on the "upper (or lower)" or "upper (or lower)" of a component means that an arbitrary element is placed in contact with the upper (or lower) surface of the component. In addition, it may mean that other components may be interposed between the component and any component disposed on (or under) the component.

As used herein, the term 'hetero' means that one or more of the carbon atoms constituting these aromatic or alicyclic rings, for example, 1 to 5 carbon atoms are N, O, S and It means substituted with one or more heteroatoms selected from the group consisting of combinations thereof.

Hereinafter, the structure and manufacturing example of the organometallic compound according to the present invention and an organic light emitting device including the same will be described.

In the organometallic compound according to one embodiment of the present invention, a structure in which a 5-membered fused ring is additionally introduced into the basic skeleton of 2-phenylquinoline is bonded to a central coordination metal. It is characterized in that it contains as a main ligand. The 5-membered fused ring additionally introduced into the 2-phenylquinoline corresponds to R in the structure of [Formula I] of the present invention.

By applying the organometallic compound having such a structure as a dopant of the light emitting layer, rigidity is imparted to the molecule of the organometallic compound, and as a result of a narrow half-width, color purity can be improved, and luminous efficiency and lifespan can be improved by reducing a non-emission recombination process. can do.

The organometallic compound according to the present invention having the above characteristics may be represented by the following formula (I).

[화학식 I]

[Formula I]

In the above formula I,

M is a central coordination metal, molybdenum (Mo), tungsten (W), rhenium (Re), ruthenium (Ru), osmium (Os), rhodium (Rh), iridium (Ir), palladium (Pd), platinum (Pt) ) and may be one selected from the group consisting of gold (Au);

R is a fused ring formed by connecting X ₁ and X ₂ ;

R ₁ and R ₂ are each independently hydrogen, deuterium, halogen, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted A substituted C3-C20 cycloalkyl group, a substituted or unsubstituted C1-C20 heteroalkyl group, a substituted or unsubstituted C7-C20 arylalkyl group, a substituted or unsubstituted C1-C20 alkenyl group, a substituted or unsubstituted C3-C20 cycloalkenyl group, substituted or unsubstituted C1-C20 heteroalkenyl group, alkynyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 heteroaryl group, alkoxy It may be one selected from the group consisting of an amino group, a silyl group, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a sulfanyl group, a sulfinyl group, a sulfonyl group, and a phosphino group;

Y is BR ₃ , CR ₃ R ₄ , C=O, CNR ₃ , SiR ₃ R ₄ , NR ₃ , PR ₃ , AsR ₃ , SbR ₃ , P(O)R ₃ , P(S)R ₃ , P( Se)R ₃ , As(O)R ₃ , As(S)R _{3 , As(Se)R 3 ,} Sb(O)R ₃ , Sb(S)R ₃ , Sb(Se)R ₃ , O, S , Se, Te, SO, SO ₂ , SeO, SeO ₂ , TeO and TeO ₂ It may be one selected from the group consisting of;

R ₃ and R ₄ are each independently hydrogen, deuterium, halogen, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted A substituted C3-C20 cycloalkyl group, a substituted or unsubstituted C1-C20 heteroalkyl group, a substituted or unsubstituted C7-C20 arylalkyl group, a substituted or unsubstituted C1-C20 alkenyl group, a substituted or unsubstituted C3-C20 cycloalkenyl group, substituted or unsubstituted C1-C20 heteroalkenyl group, alkynyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 heteroaryl group, alkoxy It may be one selected from the group consisting of an amino group, a silyl group, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a sulfanyl group, a sulfinyl group, a sulfonyl group, and a phosphino group;

X ₃ to X ₆ may each independently be one selected from CR ₅ and N;

Adjacent substituents of X ₃ to X ₆ may be fused to form a ring, and the ring may be a C5-C6 carbon ring or a heterocyclic ring;

X ₇ to X ₁₀ may each independently be one selected from CR ₆ and N;

R ₅ and R ₆ are each independently hydrogen, deuterium, halogen, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted A substituted C3-C20 cycloalkyl group, a substituted or unsubstituted C1-C20 heteroalkyl group, a substituted or unsubstituted C7-C20 arylalkyl group, a substituted or unsubstituted C1-C20 alkenyl group, a substituted or unsubstituted C3-C20 cycloalkenyl group, substituted or unsubstituted C1-C20 heteroalkenyl group, alkynyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 heteroaryl group, alkoxy It may be one selected from the group consisting of an amino group, a silyl group, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a sulfanyl group, a sulfinyl group, a sulfonyl group, and a phosphino group;

는 두 자리 리간드(bidentate ligand)일 수 있고;

can be a bidentate ligand;

m may be an integer of 1, 2 or 3, n may be an integer of 0, 1 or 2, and m+n may be an oxidation number of metal M.

An organometallic compound according to an embodiment of the present invention is composed of the following Formula II-1 and Formula II-2 according to the direction in which R (5-membered fused ring) is bonded to X ₁ and X ₂ in Formula I, which is a main ligand. It may be one structure selected from the group.

[화학식 II-1]

[Formula II-1]

[화학식 II-2]

[Formula II-2]

In Formula II-1 and Formula II-2,

, m 및 n은 상기에서 기재된 정의와 동일하다.Y, R ₁ to R ₂ , X ₃ to X ₁₀ ,

, m and n have the same definitions as described above.

In the organometallic compound of Formula I according to one embodiment of the present invention, it is more preferable that an additional fused ring is formed at the phenyl group portion of 2-phenylquinoline of Formula I, and due to the introduction of such an additional fused ring, organometallic As a result of narrowing the full width at half maximum by imparting rigidity to the compound molecule, color purity can be improved. Specifically, it may be one structure selected from the group consisting of Chemical Formula III-1 and Chemical Formula III-2.

[화학식 III-1]

[Formula III-1]

[화학식 III-2]

[Formula III-2]

In Formula III-1 and Formula III-2,

X ₁₁ to X ₁₄ may each independently be one selected from CR ₇ and N;

R ₇ are each independently hydrogen, deuterium, halogen, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C3 -C20 cycloalkyl group, substituted or unsubstituted C1-C20 heteroalkyl group, substituted or unsubstituted C7-C20 arylalkyl group, substituted or unsubstituted C1-C20 alkenyl group, substituted or unsubstituted C3-C20 Cyclic alkenyl group, substituted or unsubstituted C1-C20 heteroalkenyl group, alkynyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 heteroaryl group, alkoxy group, amino group , It may be one selected from the group consisting of a silyl group, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a sulfanyl group, a sulfinyl group, a sulfonyl group, and a phosphino group;

, m 및 n은 상기에서 기재된 정의와 동일하다.Y, R ₁ to R ₂ , X ₅ to X ₁₀ ,

, m and n have the same definitions as described above.

In the organometallic compound according to one embodiment of the present invention, a bidentate ligand may be applied as an auxiliary ligand to the central coordination metal. The bidentate ligand of the present invention includes an electron donor, and the electron donor auxiliary ligand increases the electron density of the central coordination metal to reduce the energy of metal to ligand charge transfer (MLCT) and ³ MLCT to the T ₁ state. It acts to increase the contribution ratio of As a result, the organic electroluminescent device including the organic compound of the present invention can implement improved light emitting characteristics such as high light emitting efficiency and high external quantum efficiency.

Since phosphorescence can be efficiently obtained even at room temperature by using an iridium (Ir) or platinum (Pt) metal complex having a large atomic number, in the organometallic compound according to an embodiment of the present invention, the central coordination metal (M) is iridium ( It is preferably any one of Ir) or platinum (Pt), and more preferably iridium (Ir), but is not limited thereto.

Specific examples of the compound represented by Formula I of the present invention may be one selected from the group consisting of Compound 1 to Compound 291, but are not limited thereto as long as they fall within the definition of Formula I.

.

.

According to one embodiment of the present invention, the organometallic compound represented by Formula I of the present invention may be used as a red phosphor or a green phosphor.

Referring to Figure 1 according to an embodiment of the present invention, the first electrode 110; a second electrode 120 facing the first electrode 110; and an organic layer 130 disposed between the first electrode 110 and the second electrode 120. The organic layer 130 includes an emission layer 160, and the emission layer 160 may include an organometallic compound represented by Chemical Formula I. Also, in the organic light emitting device, the organic layer 130 disposed between the first electrode 110 and the second electrode 120 is sequentially formed from the first electrode 110 to the hole injection layer 140 (HIL). ), hole transfer layer (150, hole transfer layer; HTL), light emitting layer (160, emission material layer, EML), electron transport layer (170, electron transfer layer; ETL) and electron injection layer (180, electron injection layer, EIL) It may be a structure that includes A second electrode 120 may be formed on the electron injection layer 180, and a protective film (not shown) may be formed thereon.

The first electrode 110 may be an anode and may be made of ITO, IZO, tin-oxide or zinc-oxide, which is a conductive material having a relatively high work function value, but is not limited thereto.

The second electrode 120 may be a cathode and may include Al, Mg, Ca, Ag, or an alloy or combination thereof, which is a conductive material having a relatively low work function value, but is not limited thereto.

The hole injection layer 140 may be positioned between the first electrode 110 and the hole transport layer 150 . The material of the hole injection layer 140 is MTDATA, CuPc, TCTA, NPB (NPD), HATCN, TDAPB, PEDOT / PSS, N- (biphenyl-4-yl) -9,9-dimethyl-N- (4- ( 9-phenyl-9H-carbazol-3-yl) phenyl) -9H-luoren-2-amine, NPNPB (N, N'-diphenyl-N, N'-di [4- (N, N-diphenyl- amino) phenyl] benzidine), and the like, and preferably includes NPNPB, but is not limited thereto.

The hole transport layer 150 is positioned adjacent to the light emitting layer between the first electrode 110 and the light emitting layer 160 . The hole transport layer 150 is TPD, NPD, CBP, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl) -9H-fluoren-2-amine, N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)biphenyl)-4-amine, etc. It may include a compound selected from the group consisting of, but is not limited thereto.

According to the present invention, the light emitting layer 160 may be formed by doping the organometallic compound represented by Formula I as a dopant in order to improve the light emitting efficiency of the host and the device. The light emitting layer 160 may be applied by adding about 1 to 30% by weight of the organometallic compound of Formula I of the present invention to a host material, and may be used as a material that emits green or red light.

For example, the light emitting layer 160 may include any one host material selected from the group consisting of CBP (carbazole biphenyl), mCP (1,3-bis (carbazol-9-yl), etc., but is not limited thereto. .

An electron transport layer 170 and an electron injection layer 180 may be sequentially stacked between the light emitting layer 160 and the second electrode 120 . The material of the electron transport layer 170 requires high electron mobility, and electrons can be stably supplied to the light emitting layer through smooth electron transport.

For example, the material of the electron transport layer 170 is Alq3 (tris(8-hydroxyquinolino)aluminum), Liq (8-hydroxyquinolinolatolithium), PBD (2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1, 3,4oxadiazole), TAZ (3-(4-biphenyl)4-phenyl-5-tert-butylphenyl-1,2,4-triazole), spiro-PBD, BAlq (bis(2-methyl-8-quinolinolate)- 4-(phenylphenolato)aluminium), SAlq, TPBi(2,2',2-(1,3,5-benzinetriyl)-tris(1-phenyl-1-H-benzimidazole), oxadiazole, tria triazole, phenanthroline, benzoxazole, benzthiazole, ZADN (2-[4-(9,10-Di-2-naphthalen2-yl-2-anthracen-2 -yl)phenyl]-1-phenyl-1H-benzoimidazole) and the like, and preferably includes ZADN, but is not limited thereto.

The electron injection layer 180 serves to facilitate the injection of electrons, and the material of the electron injection layer is a group consisting of Alq3 (tris (8-hydroxyquinolino) aluminum), PBD, TAZ, spiro-PBD, BAlq, SAlq, etc. It may include a compound selected from, but is not limited thereto. Alternatively, the electron injection layer 180 may be made of a metal compound, and the metal compound is, for example, Liq, LiF, NaF, KF, RbF, CsF, FrF, BeF ₂ , MgF ₂ , CaF ₂ , SrF ₂ , BaF ₂ And RaF ₂ It may be any one or more selected from the group consisting of, but is not limited thereto.

The organic light emitting device according to the present invention may be used in an organic light emitting display device and a lighting device to which the organic light emitting device is applied. As an embodiment, FIG. 2 is a schematic cross-sectional view of an organic light emitting display device to which an organic light emitting device according to an exemplary embodiment of the present invention is applied.

As shown in FIG. 2 , the organic light emitting display device 3000 may include a substrate 3010, an organic light emitting device 4000, and an encapsulation film 3900 covering the organic light emitting device 4000. can A driving thin film transistor (Td) as a driving element and an organic light emitting element 4000 connected to the driving thin film transistor (Td) are positioned on the substrate 3010 .

Although not shown, on the substrate 3010, a gate line and a data line cross each other to define a pixel area, and a switching connected to a power line, a gate line, and a data line that extends in parallel and spaced apart from any one of the gate line and the data line. A storage capacitor connected to one electrode of the thin film transistor, the power wiring, and the switching thin film transistor is further formed.

The driving thin film transistor Td is connected to the switching thin film transistor and includes a semiconductor layer 3100, a gate electrode 3300, a source electrode 3520, and a drain electrode 3540.

The semiconductor layer 3100 is formed on the substrate 3010 and may be made of an oxide semiconductor material or polycrystalline silicon. When the semiconductor layer 3100 is made of an oxide semiconductor material, a light-shielding pattern (not shown) may be formed under the semiconductor layer 3100, and the light-shielding pattern prevents light from entering the semiconductor layer 3100, thereby preventing light from entering the semiconductor layer 3100. (3010) is prevented from being deteriorated by light. Alternatively, the semiconductor layer 3100 may be made of polycrystalline silicon, and in this case, both edges of the semiconductor layer 3100 may be doped with impurities.

A gate insulating film 3200 made of an insulating material is formed on the entire surface of the substrate 3010 on the semiconductor layer 3100 . The gate insulating layer 3200 may be made of an inorganic insulating material such as silicon oxide or silicon nitride.

A gate electrode 3300 made of a conductive material such as metal is formed on the gate insulating layer 3200 corresponding to the center of the semiconductor layer 3100 . The gate electrode 3300 is connected to the switching thin film transistor.

An interlayer insulating film 3400 made of an insulating material is formed on the entire surface of the substrate 3010 above the gate electrode 3300 . The interlayer insulating layer 3400 may be formed of an inorganic insulating material such as silicon oxide or silicon nitride, or an organic insulating material such as benzocyclobutene or photo-acryl.

The interlayer insulating film 3400 has first and second semiconductor layer contact holes 3420 and 3440 exposing both sides of the semiconductor layer 3100 . The first and second semiconductor layer contact holes 3420 and 3440 are spaced apart from the gate electrode 3300 on both sides of the gate electrode 3300 .

A source electrode 3520 and a drain electrode 3540 made of a conductive material such as metal are formed on the interlayer insulating film 3400 . The source electrode 3520 and the drain electrode 3540 are spaced apart from each other around the gate electrode 3300, and both sides of the semiconductor layer 3100 and each other through the first and second semiconductor layer contact holes 3420 and 3440. make contact The source electrode 3520 is connected to a power line (not shown).

The semiconductor layer 3100, the gate electrode 3300, the source electrode 3520, and the drain electrode 3540 form a driving thin film transistor (Td), and the driving thin film transistor (Td) has a gate on top of the semiconductor layer 3100. It has a coplanar structure in which the electrode 3300, the source electrode 3520, and the drain electrode 3540 are positioned.

In contrast, the driving thin film transistor Td may have an inverted staggered structure in which a gate electrode is positioned below the semiconductor layer and a source electrode and a drain electrode are positioned above the semiconductor layer. In this case, the semiconductor layer may be made of amorphous silicon. Meanwhile, the switching thin film transistor (not shown) may have substantially the same structure as that of the driving thin film transistor Td.

Meanwhile, the organic light emitting display device 3000 may include a color filter 3600 that absorbs light generated by the light emitting diode 4000 . For example, the color filter 3600 may absorb red (R), green (G), blue (B), and white (W) light. In this case, red, green, and blue color filter patterns that absorb light may be separately formed for each pixel area, and each of these color filter patterns is an organic light emitting device that emits light of a wavelength band to be absorbed. It may be arranged to overlap with the organic layer 4300 in (4000), respectively. By adopting the color filter 3600, the organic light emitting display device 3000 can implement full-color.

For example, when the organic light emitting display device 3000 is a bottom emission type, a color filter 3600 absorbing light may be positioned on the interlayer insulating layer 3400 corresponding to the organic light emitting device 4000 . In an optional embodiment, when the organic light emitting display device 3000 is a top emission type, the color filter may be positioned above the organic light emitting device 4000, that is, above the second electrode 4200. For example, the color filter 3600 may be formed to a thickness of 2 μm to 5 μm.

Meanwhile, a protective layer 3700 having a drain contact hole 3720 exposing the drain electrode 3540 of the driving thin film transistor Td is formed to cover the driving thin film transistor Td.

On the protective layer 3700, a first electrode 4100 connected to the drain electrode 3540 of the driving thin film transistor Td through the drain contact hole 3720 is formed separately for each pixel area.

The first electrode 4100 may be an anode and may be made of a conductive material having a relatively high work function value. For example, the first electrode 410 is ITO. It may be made of a transparent conductive material such as IZO or ZnO.

Meanwhile, when the organic light emitting display device 3000 is a top-emission type, a reflective electrode or a reflective layer may be further formed below the first electrode 4100 . For example, the reflective electrode or the reflective layer may be made of any one of aluminum (Al), silver (Ag), nickel (Ni), and aluminum-palladium-copper (APC) alloy.

A bank layer 3800 covering an edge of the first electrode 4100 is formed on the passivation layer 3700 . The bank layer 3800 exposes the center of the first electrode 4100 corresponding to the pixel area.

An organic layer 4300 is formed on the first electrode 4100, and the organic light emitting device 4000 may have a tandem structure if necessary.

A second electrode 4200 is formed on the substrate 3010 on which the organic layer 4300 is formed. The second electrode 4200 is located on the front surface of the display area and is made of a conductive material having a relatively low work function value and can be used as a cathode. For example, the second electrode 4200 may be formed of any one of aluminum (Al), magnesium (Mg), and aluminum-magnesium alloy (AlMg).

The first electrode 4100, the organic layer 4300, and the second electrode 4200 form the organic light emitting device 4000.

An encapsulation film 3900 is formed on the second electrode 4200 to prevent penetration of external moisture into the organic light emitting device 4000 . Although not shown, the encapsulation film 3900 may have a three-layer structure in which a first inorganic layer, an organic layer, and an inorganic layer are sequentially stacked, but is not limited thereto.

The organic light emitting device of the present invention may be a white light emitting diode having a tandem structure. In the case of a tandem organic light emitting device according to an embodiment of the present invention, a single light emitting device (EL Unit) may be formed in a structure in which two or more are connected by a charge generation layer (CGL). The organic light emitting device includes a first electrode and a second electrode facing each other on a substrate and two or more plurality of light emitting units (stack) having a light emitting layer stacked between the first and second electrodes to emit light in a specific wavelength range. ; stack). At this time, at least one of the light emitting layers may include an organometallic compound represented by Formula I according to the present invention as a dopant. The plurality of light emitting units in the tandem structure may be connected to a charge generating layer (CGL) composed of an N-type charge generating layer and a P-type charge generating layer.

5, which is an embodiment of the present invention, is a schematic cross-sectional view of an organic light emitting device having a tandem structure having two light emitting units. As shown in FIG. 5, the organic light emitting device 100 of the present invention includes a first electrode 110 and a second electrode 120 facing each other, and a first electrode 110 and a second electrode 120 It includes an organic layer 230 positioned between them. The organic layer 230 is positioned between the first electrode 110 and the second electrode 120 and includes the first light emitting parts ST1 and 240 including the first light emitting layer 161 and the first light emitting part 240. The second light emitting part (ST2, 250) located between the second electrode 120 and including the second light emitting layer 162, and the charge generation layer (positioned between the first and second light emitting parts 240, 250) CGL, 260). The charge generation layer may include an N-type charge generation layer 191 and a P-type charge generation layer 192 .

In addition, the organic light emitting device according to one embodiment of the present invention may be a tandem organic light emitting device having three light emitting units, and furthermore, four or more light emitting units and three light emitting units are provided between the first electrode and the second electrode. The above charge generation layer may be disposed.

Hereinafter, synthesis examples and examples of the present invention will be described. However, the following examples are only examples of the present invention, but are not limited thereto.

synthesis example

<Preparation of Compound A1>

Step 1) Preparation of Compound A1-1

2-bromothiophene (25.6g, 157.14mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (41.6g, 190.01mmol), Pd( PPh ₃ ) ₄ (9.2g, 7.92 mmol) and NaHCO ₃ (39.9g, 288.76mmol) were dissolved in 1,4-dioxane (500ml) and distilled water (100ml) and refluxed for 15 hours. After completion of the reaction, the mixture was cooled to room temperature and extracted using MC (methylene chloride) and distilled water. After water was removed by adding MgSO ₄ to the organic layer, the solvent was removed by filtration under reduced pressure. Column chromatography with hexane and MC gave compound A1-1 (26.8g, yield 96%).

MS (m/z): 175.25

Step 2) Preparation of Compound A1-2

A1-1 (26.8g, 152.64mmol), ethyl chloroforme (5.16ml, 53.92mmol) and K2CO3 (40.6g, 305.28mmol) were dissolved in chloroform (500ml) in a reaction vessel and refluxed for 18 hours. After completion of the reaction, the mixture was cooled to room temperature and extracted using MC and distilled water. After water was removed by adding MgSO ₄ to the organic layer, the solvent was removed by filtration under reduced pressure. Hexane and MC were subjected to column chromatography to obtain compound A1-2 (36.71 g, yield 97%).

MS (m/z): 247.31

Step 3) Preparation of Compound A1

A1-2 (33.3g, 134.9mmol), POCl3 (126ml, 1346.89mmol) and 30ml of TEA were added to the reaction vessel and refluxed for 16 hours. After cooling the reaction solution to room temperature, extraction was performed using MC and distilled water. After water was removed by adding MgSO ₄ to the organic layer, the solvent was removed by filtration under reduced pressure. The mixture was dissolved in EA and filtered under reduced pressure after a silica gel filter to remove the solvent. The obtained solid was slurried with hexane to obtain Compound A1 (11.2 g, yield 38%) in the form of an ivory solid.

MS (m/z): 219.69

<Preparation of Compound A2>

Step 1) Preparation of Compound A2-1

After dissolving 2-methylfuran (30.1 g, 366.626 mol) in chloroform in the reaction vessel, the temperature was lowered to -20 ° C, and NBS (65.3 g, 366.626 mmol) was slowly added dropwise. After raising the reaction solution to room temperature, it was stirred for 30 minutes. After completion of the reaction, extraction was performed using MC and distilled water. After water was removed by adding MgSO ₄ to the organic layer, the solvent was removed by filtration under reduced pressure. The mixture was dissolved in hexane and filtered through silica gel to obtain compound A2-1 (39g, yield 66%) in a transparent liquid form.

MS (m/z) : 161.00

Step 2) Preparation of Compound A2-2

A2-1 (33.2g, 206.40mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (54.3g, 247.68mmol), Pd( PPh ₃ ) ₄ (11.9g, 10.32mmol) and NaHCO ₃ (85.6g, 619.19mmol) were dissolved in 1,4-dioxane (500ml) and distilled water (100ml) and refluxed for 15 hours. After completion of the reaction, the mixture was cooled to room temperature and extracted using MC and distilled water. After water was removed by adding MgSO ₄ to the organic layer, the solvent was removed by filtration under reduced pressure. Column chromatography with hexane and MC gave compound A2-2 (17.7g, yield 49%).

MS (m/z): 173.21

Step 3) Preparation of Compound A2-3

A2-2 (17.7g, 102.02mmol), ethyl chloroforme (11.7ml, 122.42mmol) and K ₂ CO ₃ (28.2g, 204.03mmol) were dissolved in chloroform (300ml) and refluxed for 18 hours. After completion of the reaction, the mixture was cooled to room temperature and extracted using MC and distilled water. After water was removed by adding MgSO ₄ to the organic layer, the solvent was removed by filtration under reduced pressure. Hexane and MC were subjected to column chromatography to obtain compound A2-3 (20.6 g, yield 82%).

MS (m/z): 245.27

Step 4) Preparation of Compound A2

A2-3 (20.6g, 83.99mmol), POCl ₃ (78.5ml, 839.89mmol) and TEA (20ml) were added to the reaction vessel and refluxed for 16 hours. After cooling the reaction solution to room temperature, extraction was performed using MC and distilled water. After water was removed by adding MgSO ₄ to the organic layer, the solvent was removed by filtration under reduced pressure. The mixture was dissolved in EA and filtered under reduced pressure after a silica gel filter to remove the solvent. The obtained solid was slurried with hexane to obtain Compound A2 (8.4 g, yield 46%) in the form of an ivory solid.

MS (m/z): 217.65

<Preparation of Compound B1>

A1 (11g, 50.07mmol), (3,5-dimethylphenyl)boronic acid (8.3g, 55.08mmol), Pd(PPh ₃ ) ₄ (5.7g, 5.01mmol) and K ₂ CO ₃ (13.8g, 100.14mmol) was dissolved in 1,4-dioxane (150ml) and distilled water (30ml) and refluxed for 16 hours. After completion of the reaction, the mixture was cooled to room temperature and extracted using MC and distilled water. After water was removed by adding MgSO ₄ to the organic layer, the solvent was removed by filtration under reduced pressure. Column chromatography with hexane and MC gave compound B1 (10.6 g, yield 73%).

MS (m/z): 289.39

<Preparation of Compound B2>

A2 (8 g, 36.77 mmol), 2-(4-(tert-butyl)naphthalen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (12.5 g, 40.43 mmol), Pd(PPh ₃ ) ₄ (4.2g, 3.68mmol) and K ₂ CO ₃ (10.2g, 73.51mmol) were dissolved in 1,4-dioxane (120ml) and distilled water (24ml) and refluxed for 16 hours. . After completion of the reaction, the mixture was cooled to room temperature and extracted using MC and distilled water. After water was removed by adding MgSO ₄ to the organic layer, the solvent was removed by filtration under reduced pressure. Column chromatography with hexane and MC gave compound B2 (9.8g, yield 73%).

MS (m/z): 365.47

<Preparation of Compound 42>

Preparation of compound C1

B1 (10g, 34.55mmol), 200ml of 2-ethoxyethanol, and 66ml of distilled water were added to the reaction container, and nitrogen was bubbled for 1 hour. Then, IrCl ₃ and H ₂ O (6.1g, 15.71mmol) were added and refluxed for 24 hours. After the reaction was completed, the temperature was slowly lowered to room temperature, and the resulting solid was filtered. The filtered solid was washed with methanol and dried to obtain compound C1 (10.1g, yield 80%).

Preparation of compound 42

C1 (10.1g, 6.28mmol), 3,7-diethylnonane-4,6-dione (12.7g, 59.64mmol), Na ₂ CO ₃ (13g, 122.46mmol), and 300ml of 2-ethoxyethanol were added to the reaction vessel and 24 Stir gently for an hour. After the reaction was completed, dichloromethane was added to the reactant to dissolve the reaction product, and then extracted with dichloromethane and distilled water. After removing water from the organic layer using MgSO ₄ and filtering, the solvent was removed under reduced pressure. Column chromatography with hexane and dichloromethane gave compound 42 (5.2g, yield 43%).

MS (m/z) : 966.28

<Preparation of Compound 5>

Preparation of compound C3

B3 (6.0g, 22mmol), IrCl ₃ .H ₂ Ox (3.5g, 10mmol) instead of B1 (10g, 34.55mmol) and IrCl ₃ .H ₂ Ox (6.1g, 15.71mmol) in the preparation method of Compound C1 Compound C3 (6.4g, yield 83%) was obtained in the same manner except for the above.

Preparation of compound 5

In the preparation method of Compound 42, C1 (10.1g, 6.28mmol), 3,7-diethylnonane-4,6-dione (12.7g, 59.64mmol), Na ₂ CO ₃ (13g, 122.46mmol) instead of C3 (6.4g, 4.15mmol), pentane-2,4-dione (4.2g, 41.50mmol), and Na ₂ CO ₃ (8.8g, 83mmol) were used, but Compound 5 (3.5g, 50% yield) was obtained in the same manner. .

MS (m/z) : 836.22

<Preparation of Compound 7>

Preparation of compound C4

B4 (5.8g, 22mmol), IrCl ₃ .H ₂ Ox (3.5g, 10mmol) instead of B1 (10g, 34.55mmol) and IrCl ₃ .H ₂ Ox (6.1g, 15.71mmol) in the preparation method of Compound C1 Compound C4 (5.3g, yield 70%) was obtained in the same manner except for the above.

Preparation of compound 7

In the preparation method of Compound 42, C4 ( _5.3 g _, 5.3 g, 3.50mmol), pentane-2,4-dione (3.5g, 35.00mmol), and Na ₂ CO ₃ (7.4g, 70mmol) were used, but Compound 7 (2.3g, 40% yield) was obtained in the same manner. .

MS (m/z) : 816.14

<Preparation of Compound 8>

Preparation of compound C5

B5 (7.0g, 22mmol), IrCl ₃ .H ₂ Ox (3.5g, 10mmol) instead of B1 (10g, 34.55mmol) and IrCl ₃ .H ₂ Ox (6.1g, 15.71mmol) in the preparation method of compound C1 Compound C5 (6.7g, yield 78%) was obtained in the same manner except for the above.

Preparation of compound 8

In the preparation method of Compound 42, C5 (6.7g, _{6.7g ,} 3.90mmol), pentane-2,4-dione (3.9g, 39.00mmol), and Na ₂ CO ₃ (8.3g, 78mmol) were used, but Compound 8 (3.0g, 41% yield) was obtained in the same manner. .

MS (m/z) : 924.24

<Preparation of Compound 10>

Preparation of compound C6

B6 (6.0g, 22mmol), IrCl ₃ .H ₂ Ox (3.5g, 10mmol) instead of B1 (10g, 34.55mmol) and IrCl ₃ .H ₂ Ox (6.1g, 15.71mmol) in the preparation method of Compound C1 Compound C6 (6.4g, yield 83%) was obtained in the same manner except for the above.

Preparation of compound 10

In the preparation method of Compound 42, C6 (6.4g, _{6.4g ,} 4.15mmol), 3,7-diethylnonane-4,6-dione (8.8g, 41.50mmol), and Na ₂ CO ₃ (8.8g, 83mmol) were used, but Compound 10 (3.4g, yield 43) was obtained in the same manner. %) was obtained.

MS (m/z) : 948.35

<Preparation of Compound 11>

Preparation of compound C7

B7 (6.0g, 22mmol), IrCl ₃ .H ₂ Ox (3.5g, 10mmol) instead of B1 (10g, 34.55mmol) and IrCl ₃ .H ₂ Ox (6.1g, 15.71mmol) in the preparation method of Compound C1 Compound C7 (6.4g, yield 83%) was obtained in the same manner except for the above.

Preparation of compound 11

In the preparation method of Compound 42, C7 ( _6.4g , 6.4g _, 4.15mmol), 3,7-diethyl-3,7-dimethylnonane-4,6-dione (10.0g, 41.50mmol), and Na ₂ CO ₃ (8.8g, 83mmol) were used, but Compound 11 was prepared in the same manner. (3.4 g, yield 42%) was obtained.

MS (m/z) : 976.38

<Preparation of Compound 15>

Preparation of compound C8

B8 (6.0g, 22mmol), IrCl ₃ .H ₂ Ox (3.5g, 10mmol) instead of B1 (10g, 34.55mmol) and IrCl ₃ .H ₂ Ox (6.1g, 15.71mmol) in the preparation method of Compound C1 Compound C8 (6.4g, yield 83%) was obtained in the same manner except for the above.

Preparation of compound 15

In the preparation method of Compound 42, C8 (6.4g, _{6.4g ,} 4.15mmol), (E)-4-(isopropylimino)pentan-2-one (5.9g, 41.50mmol), and Na ₂ CO ₃ (8.8g, 83mmol) were used, but Compound 15 (2.9g , yield 40%) was obtained.

MS (m/z): 877.29

<Preparation of Compound 16>

Preparation of compound C9

B9 (6.0g, 22mmol), IrCl ₃ .H ₂ Ox (3.5g, 10mmol) instead of B1 (10g, 34.55mmol) and IrCl ₃ .H ₂ Ox (6.1g, 15.71mmol) in the preparation method of Compound C1 Compound C9 (6.4g, yield 83%) was obtained in the same manner except for the above.

Preparation of compound 16

In the preparation method of Compound 42, C1 (10.1g, 6.28mmol), 3,7-diethylnonane-4,6-dione (12.7g, 59.64mmol), Na ₂ CO ₃ (13g, 122.46mmol) instead of C9 (6.4g, 4.15mmol), (E) -N,N'-diisopropylbenzimidamide (8.5g, 41.50mmol), and Na ₂ CO ₃ (8.8g, 83mmol) were used, but Compound 16 (2.9g, yield 37%) was obtained in the same manner. ) was obtained.

MS (m/z): 940.33

<Preparation of Compound 19>

Preparation of compound C10

B1 (10g, 34.55mmol), IrCl ₃ .H ₂ Ox (6.1g, 15.71mmol) in the preparation method of compound C1 B10 (7.2g, 22mmol), IrCl ₃ .H ₂ Ox (3.5g, 10mmol) was used Compound C10 (6.6g, yield 75%) was obtained in the same manner except for the above.

Preparation of compound 19

In the preparation method of compound 42, C1 (10.1g, 6.28mmol), 3,7-diethylnonane-4,6-dione (12.7g, 59.64mmol), Na ₂ CO ₃ (13g, 122.46mmol) instead of C10 (6.6g, 3.75mmol), 3,7-diethyl-3,7-dimethylnonane-4,6-dione (9.0g, 37.50mmol), and Na ₂ CO ₃ (7.9g, 75mmol) were used, but Compound 19 was prepared in the same manner. (3.3 g, yield 41%) was obtained.

MS (m/z) : 1088.50

<Preparation of Compound 21>

Preparation of compound C11

B1 (10g, 34.55mmol), IrCl ₃ .H ₂ Ox (6.1g, 15.71mmol) in the preparation method of compound C1 instead of B11 (7.4g, 22mmol), IrCl ₃ .H ₂ Ox (3.5g, 10mmol) Compound C11 (6.7g, yield 74%) was obtained in the same manner except for the above.

Preparation of compound 21

In the preparation method of Compound 42, C1 (10.1g, 6.28mmol), 3,7-diethylnonane-4,6-dione (12.7g, 59.64mmol), Na ₂ CO ₃ (13g, 122.46mmol) instead of C11 (6.7g, 3.70mmol), 3,7-diethyl-3,7-dimethylnonane-4,6-dione (8.9g, 37.00mmol), and Na ₂ CO ₃ (7.8g, 74mmol) were used, but Compound 21 was prepared in the same manner. (3.4 g, yield 41%) was obtained.

MS (m/z) : 1104.60

<Preparation of Compound 28>

Preparation of compound C12

B1 (10g, 34.55mmol), IrCl ₃ .H ₂ Ox (6.1g, 15.71mmol) in the preparation method of compound C1 B12 (8.2g, 22mmol), IrCl ₃ .H ₂ Ox (3.5g, 10mmol) was used Compound C12 (6.8g, yield 70%) was obtained in the same manner except for the above.

Preparation of compound 28

In the preparation method of compound 42, C1 (10.1g, 6.28mmol), 3,7-diethylnonane-4,6-dione (12.7g, 59.64mmol), Na ₂ CO ₃ (13g, 122.46mmol) instead of C12 (6.8g, 3.50mmol), 3,7-diethyl-3,7-dimethylnonane-4,6-dione (8.4g, 35.00mmol), and Na ₂ CO ₃ (7.4g, 70mmol) were used, but Compound 28 was prepared in the same manner. (3.3 g, yield 40%) was obtained.

MS (m/z) : 1172.60

<Preparation of Compound 32>

Preparation of compound C13

B1 (10g, 34.55mmol), IrCl ₃ .H ₂ Ox (6.1g, 15.71mmol) in the preparation method of compound C1 B13 (5.7g, 22mmol), IrCl ₃ .H ₂ Ox (3.5g, 10mmol) was used Compound C13 (5.1 g, yield 68%) was obtained in the same manner except for the above.

Preparation of compound 32

In the preparation method of compound 42, C1 (10.1g, 6.28mmol), 3,7-diethylnonane-4,6-dione (12.7g, 59.64mmol), Na ₂ CO ₃ (13g, 122.46mmol) instead of C13 (5.1g, Compound ₃₂ ( _2.5 g, yield 40 %) was obtained.

MS (m/z) : 924.30

<Preparation of Compound 83>

Preparation of compound C14

B1 (10g, 34.55mmol), IrCl ₃ .H ₂ Ox (6.1g, 15.71mmol) in the preparation method of compound C1 B14 (7.2g, 22mmol), IrCl ₃ .H ₂ Ox (3.5g, 10mmol) was used Compound C14 (6.6g, yield 75%) was obtained in the same manner except for the above.

Preparation of compound 83

In the preparation method of compound 42, C1 (10.1g, 6.28mmol), 3,7-diethylnonane-4,6-dione (12.7g, 59.64mmol), Na ₂ CO ₃ (13g, 122.46mmol) instead of C14 (6.6g, 3.75mmol), 3,7-diethyl-3,7-dimethylnonane-4,6-dione (9.0g, 37.50mmol), and Na ₂ CO ₃ (7.9g, 75mmol) were used, but Compound 83 was prepared in the same manner. (3.3 g, yield 41%) was obtained.

MS (m/z) : 1088.50

<Preparation of Compound 115>

Preparation of compound C15

B1 (10g, 34.55mmol), IrCl ₃ .H ₂ Ox (6.1g, 15.71mmol) in the preparation method of compound C1 B15 (7.6g, 22mmol), IrCl ₃ .H ₂ Ox (3.5g, 10mmol) was used Compound C15 (6.6g, yield 72%) was obtained in the same manner except for the above.

Preparation of compound 115

In the preparation method of Compound 42, C1 (10.1g, 6.28mmol), 3,7-diethylnonane-4,6-dione (12.7g, 59.64mmol), Na ₂ CO ₃ (13g, 122.46mmol) instead of C15 (6.6g, 3.60mmol), 3,7-diethyl-3,7-dimethylnonane-4,6-dione (8.7g, 36.00mmol), and Na ₂ CO ₃ (7.9g, 75mmol) were used, but Compound 115 was prepared in the same manner. (3.1 g, yield 39%) was obtained.

MS (m/z) : 1088.50

<Preparation of Compound 145>

Preparation of compound C2

B2 (9g, 24.63mmol), 200ml of 2-ethoxyethanol, and 66ml of distilled water were added to the reaction container, and nitrogen was bubbled for 1 hour. Then, IrCl ₃ ,H ₂ O (4.3g, 11.19mmol) was added and refluxed for 24 hours. After the reaction was completed, the temperature was slowly lowered to room temperature, and the resulting solid was filtered. The filtered solid was washed with methanol and dried to obtain compound C2 (4.9g, yield 46%).

Preparation of compound 145

C2 (4.9g, 2.56mmol), 3,7-diethylnonane-4,6-dione (5.3g, 24.98mmol), Na ₂ CO ₃ (5.3g, 49.92mmol), and 200ml of 2-ethoxyethanol were added to the reaction vessel. Stir gently for 24 hours. After the reaction was completed, dichloromethane was added to the reactant to dissolve the reaction product, and then extracted with dichloromethane and distilled water. After removing water from the organic layer using MgSO ₄ and filtering, the solvent was removed under reduced pressure. Column chromatography with hexane and dichloromethane gave compound 145 (2.7g, yield 60%).

MS (m/z): 1132.46

<Preparation of Compound 131>

Preparation of compound C16

B16 (7.7g, 22mmol), IrCl ₃ .H ₂ Ox (3.5g, 10mmol) instead of B2 (9g, 24.63mmol) and IrCl ₃ .H ₂ Ox (4.3g, 11.19mmol) in the preparation method of compound C2 Compound C16 (4.1g, yield 44%) was obtained in the same manner except for the above.

Preparation of compound 131

In the preparation method of compound 42, C2 (4.9g, 2.56mmol), 3,7-diethylnonane-4,6-dione (5.3g, 24.98mmol), Na ₂ CO ₃ (5.3g, 49.92mmol) instead of C16 (4.1g) , 2.20mmol), pentane-2,4-dione (2.2g, 22.00mmol), and Na ₂ CO ₃ (4.7g, 44mmol), but compound 131 (2.8g, yield 65%) was obtained in the same manner. Got it.

MS (m/z) : 992.32

<Preparation of Compound 135>

Preparation of compound C17

B17 (6.9g, 22mmol), IrCl ₃ .H ₂ Ox (3.5g, 10mmol) instead of B2 (9g, 24.63mmol) and IrCl ₃ .H ₂ Ox (4.3g, 11.19mmol) in the preparation method of compound C2 Compound C17 (3.4g, yield 40%) was obtained in the same manner except for the above.

Preparation of compound 135

In the preparation method of compound 42, C2 (4.9g, 2.56mmol), 3,7-diethylnonane-4,6-dione (5.3g, 24.98mmol), Na ₂ CO ₃ (5.3g, 49.92mmol) instead of C17 (3.4g) , 2.00mmol), pentane-2,4-dione (2.0g, 20.00mmol), and Na ₂ CO ₃ (4.2g, 40mmol) were used, but Compound 135 (2.0g, yield 55%) was obtained in the same manner. Got it.

MS (m/z): 916.17

<Preparation of Compound 136>

Preparation of compound C18

In the preparation method of compound C2, B18 (8.1g, 22mmol) and IrCl ₃ .H ₂ Ox (3.5g, 10mmol) were used instead of B2 (9g, 24.63mmol) and IrCl ₃ .H ₂ Ox (4.3g, 11.19mmol). Compound C18 (4.1g, yield 43%) was obtained in the same manner except for the above.

Preparation of compound 136

In the preparation method of Compound 42, C2 (4.9g, 2.56mmol), 3,7-diethylnonane-4,6-dione (5.3g, 24.98mmol), Na ₂ CO ₃ (5.3g, 49.92mmol) instead of C18 (4.1g) , 2.15mmol), pentane-2,4-dione (2.2g, 21.50mmol), and Na ₂ CO ₃ (4.6g, 43mmol), but Compound 136 (2.7g, yield 62%) was obtained in the same manner. Got it.

MS (m/z) : 1024.27

<Preparation of Compound 138>

Preparation of compound C19

B2 (9g, 24.63mmol), IrCl ₃ .H ₂ Ox (4.3g, 11.19mmol) in the preparation method of compound C2 B19 (7.7g, 22mmol), IrCl ₃ .H ₂ Ox (3.5g, 10mmol) was used Compound C19 (4.1g, yield 44%) was obtained in the same manner except for the above.

Preparation of compound 138

In the preparation method of Compound 42, C2 (4.9g, 2.56mmol), 3,7-diethylnonane-4,6-dione (5.3g, 24.98mmol), Na ₂ CO ₃ (5.3g, 49.92mmol) instead of C19 (4.1g) Compound ₁₃₈ (3.0 _g , yield 61%) was obtained.

MS (m/z): 1104.44

<Preparation of Compound 139>

Preparation of compound C20

In the preparation method of compound C2, B20 (7.7g, 22mmol) and IrCl ₃ .H ₂ Ox (3.5g, 10mmol) were used instead of B2 (9g, 24.63mmol) and IrCl ₃ .H ₂ Ox (4.3g, 11.19mmol). Compound C20 (4.1g, yield 44%) was obtained in the same manner except for the above.

Preparation of compound 139

In the preparation method of compound 42, C2 (4.9g, 2.56mmol), 3,7-diethylnonane-4,6-dione (5.3g, 24.98mmol), Na ₂ CO ₃ (5.3g, 49.92mmol) instead of C20 (4.1g) , 2.20mmol), 3,7-diethyl-3,7-dimethylnonane-4,6-dione (5.3g, 22.00mmol), and Na ₂ CO ₃ (4.7g, 44mmol) were used, but the compound was prepared in the same manner. 139 (3.0 g, yield 60%) was obtained.

MS (m/z): 1132.47

<Preparation of Compound 143>

Preparation of compound C21

In the preparation method of compound C2, B21 (7.7g, 22mmol) and IrCl ₃ .H ₂ Ox (3.5g, 10mmol) were used instead of B2 (9g, 24.63mmol) and IrCl ₃ .H ₂ Ox (4.3g, 11.19mmol). Compound C21 (4.1g, yield 44%) was obtained in the same manner except for the above.

Preparation of compound 143

In the preparation method of compound 42, C2 (4.9g, 2.56mmol), 3,7-diethylnonane-4,6-dione (5.3g, 24.98mmol), Na ₂ CO ₃ (5.3g, 49.92mmol) instead of C21 (4.1g) Compound ₁₄₃ ( _2.4 g, yield 52%) was obtained.

MS (m/z) : 1033.38

<Preparation of Compound 144>

Preparation of compound C22

B2 (9g, 24.63mmol), IrCl ₃ .H ₂ Ox (4.3g, 11.19mmol) in the preparation method of compound C2 B22 (7.7g, 22mmol), IrCl ₃ .H ₂ Ox (3.5g, 10mmol) was used Compound C22 (4.1g, yield 44%) was obtained in the same manner except for the above.

Preparation of compound 144

In the preparation method of compound 42, C2 (4.9g, 2.56mmol), 3,7-diethylnonane-4,6-dione (5.3g, 24.98mmol), Na ₂ CO ₃ (5.3g, 49.92mmol) instead of C22 (4.1g) , 2.20mmol), (E) -N,N'-diisopropylbenzimidamide (4.5g, 22.00mmol), and Na ₂ CO ₃ (4.7g, 44mmol), except for using Compound 144 (1.9g, yield 40). %) was obtained.

MS (m/z): 1096.39

<Preparation of Compound 147>

Preparation of compound C23

B2 (9g, 24.63mmol), IrCl ₃ .H ₂ Ox (4.3g, 11.19mmol) in the preparation method of compound C2 B23 (9.0g, 22mmol), IrCl ₃ .H ₂ Ox (3.5g, 10mmol) was used Compound C23 (5.2g, yield 50%) was obtained in the same manner except for the above.

Preparation of compound 147

In the preparation method of Compound 42, C2 (4.9g, 2.56mmol), 3,7-diethylnonane-4,6-dione (5.3g, 24.98mmol), Na ₂ CO ₃ (5.3g, 49.92mmol) instead of C23 (5.2g) , 2.50mmol), 3,7-diethyl-3,7-dimethylnonane-4,6-dione (6.0g, 25.00mmol), and Na ₂ CO ₃ (5.3g, 50mmol), except for using the same compound method. 147 (3.6 g, yield 58%) was obtained.

MS (m/z): 1244.60

<Preparation of Compound 149>

Preparation of compound C24

In the method for preparing compound C2, B24 (9.2g, 22mmol) and IrCl ₃ .H ₂ Ox (3.5g, 10mmol) were used instead of B2 (9g, 24.63mmol) and IrCl ₃ .H ₂ Ox (4.3g, 11.19mmol). Compound C24 (5.2 g, yield 49%) was obtained in the same manner except for the above.

Preparation of compound 149

In the preparation method of compound 42, C2 (4.9g, 2.56mmol), 3,7-diethylnonane-4,6-dione (5.3g, 24.98mmol), Na ₂ CO ₃ (5.3g, 49.92mmol) instead of C24 (5.2g) , 2.45mmol), 3,7-diethyl-3,7-dimethylnonane-4,6-dione (5.9g, 24.50mmol), and Na ₂ CO ₃ (5.2g, 49mmol), except for using the same compound method. 149 (3.5 g, yield 57%) was obtained.

MS (m/z) : 1266.74

<Preparation of Compound 156>

Preparation of compound C25

In the preparation method of compound C2, B25 (9.9g, 22mmol) and IrCl ₃ .H ₂ Ox (3.5g, 10mmol) were used instead of B2 (9g, 24.63mmol) and IrCl ₃ .H ₂ Ox (4.3g, 11.19mmol). Compound C25 (5.8g, yield 52%) was obtained in the same manner except for the above.

Preparation of compound 156

In the preparation method of Compound 42, C2 (4.9g, 2.56mmol), 3,7-diethylnonane-4,6-dione (5.3g, 24.98mmol), Na ₂ CO ₃ (5.3g, 49.92mmol) instead of C25 (5.8g) , 2.60mmol), 3,7-diethyl-3,7-dimethylnonane-4,6-dione (6.2g, 26.00mmol), and Na ₂ CO ₃ (5.5g, 52mmol), except for using the same compound method. 156 (4.1 g, yield 60%) was obtained.

MS (m/z): 1328.69

<Preparation of Compound 160>

Preparation of compound C26

B2 (9g, 24.63mmol), IrCl ₃ .H ₂ Ox (4.3g, 11.19mmol) in the preparation method of compound C2 B26 (8.1g, 22mmol), IrCl ₃ .H ₂ Ox (3.5g, 10mmol) was used Compound C26 (3.7g, yield 38%) was obtained in the same manner except for the above.

Preparation of compound 160

In the preparation method of compound 42, C2 (4.9g, 2.56mmol), 3,7-diethylnonane-4,6-dione (5.3g, 24.98mmol), Na ₂ CO ₃ (5.3g, 49.92mmol) instead of C26 (3.7g) , 1.90mmol), 3,7-diethylnonane-4,6-dione (4.0g, 19.00mmol), and Na ₂ CO ₃ (4.0g, 38mmol) were used, but Compound 160 (2.2g, yield) was obtained in the same manner. 50%) was obtained.

MS (m/z): 1136.45

<Preparation of Compound 177>

Preparation of compound C27

In the method for preparing compound C2, B27 (8.4g, 22mmol) and IrCl ₃ .H ₂ Ox (3.5g, 10mmol) were used instead of B2 (9g, 24.63mmol) and IrCl ₃ .H ₂ Ox (4.3g, 11.19mmol). Compound C27 (4.7 g, yield 48%) was obtained in the same manner except for the above.

Preparation of compound 177

In the preparation method of compound 42, C2 (4.9g, 2.56mmol), 3,7-diethylnonane-4,6-dione (5.3g, 24.98mmol), Na ₂ CO ₃ (5.3g, 49.92mmol) instead of C27 (4.7g) , 2.40mmol), 3,7-diethylnonane-4,6-dione (5.1g, 24.00mmol), and Na ₂ CO ₃ (5.1g, 48mmol), but using the same method as Compound 177 (3.1g, yield) 55%) was obtained.

MS (m/z): 1164.43

<Preparation of Compound 211>

Preparation of compound C28

In the preparation method of compound C2, B28 (9.0g, 22mmol) and IrCl ₃ .H ₂ Ox (3.5g, 10mmol) were used instead of B2 (9g, 24.63mmol) and IrCl ₃ .H ₂ Ox (4.3g, 11.19mmol). Compound C28 (4.6g, yield 44%) was obtained in the same manner except for the above.

Preparation of compound 211

In the preparation method of compound 42, C2 (4.9g, 2.56mmol), 3,7-diethylnonane-4,6-dione (5.3g, 24.98mmol), Na ₂ CO ₃ (5.3g, 49.92mmol) instead of C28 (4.6g) , 2.20mmol), 3,7-diethyl-3,7-dimethylnonane-4,6-dione (5.3g, 22.00mmol), and Na ₂ CO ₃ (4.7g, 44mmol) were used, but the compound was prepared in the same manner. 211 (3.4 g, yield 62%) was obtained.

MS (m/z): 1244.60

<Preparation of Compound 245>

Preparation of compound C29

B2 (9g, 24.63mmol), IrCl ₃ .H ₂ Ox (4.3g, 11.19mmol) in the preparation method of compound C2 B29 (9.6g, 22mmol), IrCl ₃ .H ₂ Ox (3.5g, 10mmol) was used Compound C29 (5.1 g, yield 47%) was obtained in the same manner except for the above.

Preparation of compound 245

In the preparation method of compound 42, C2 (4.9g, 2.56mmol), 3,7-diethylnonane-4,6-dione (5.3g, 24.98mmol), Na ₂ CO ₃ (5.3g, 49.92mmol) instead of C29 (5.1g) , 2.35mmol), 3,7-diethyl-3,7-dimethylnonane-4,6-dione (5.6g, 23.50mmol), and Na ₂ CO ₃ (5.0g, 47mmol), except for using the same compound method. 245 (3.7 g, yield 60%) was obtained.

MS (m/z): 1298.69

Example

<Example 1>

The glass substrate coated with ITO (indium tin oxide) to a thickness of 1,000 Å was washed, ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, and dried.

HI-1 was thermally vacuum deposited to a thickness of 60 nm as a hole injection material on the prepared ITO transparent electrode, and then NPB was thermally vacuum deposited to a thickness of 80 nm as a hole transport material. Compound 5 as a dopant and CBP as a host were used as the light emitting layer on the transport material, and thermal vacuum deposition was performed at a doping concentration of 5% and a thickness of 30 nm. ET-1: Liq (1:1) (30 nm) was thermally vacuum deposited on the light emitting layer as a material for the electron transport layer and the electron injection layer, and then 100 nm thick aluminum was deposited to form a cathode to form an organic light emitting device. produced. The materials used in Example 1 are as follows.

In the material, HI-1 is NPNPB and ET-1 is ZADN.

<Example 2>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 7 was used instead of Compound 5 in Example 1.

<Example 3>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 8 was used instead of Compound 5 in Example 1.

<Example 4>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 10 was used instead of Compound 5 in Example 1.

<Example 5>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 11 was used instead of Compound 5 in Example 1.

<Example 6>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 15 was used instead of Compound 5 in Example 1.

<Example 7>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 16 was used instead of Compound 5 in Example 1.

<Example 8>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 19 was used instead of Compound 5 in Example 1.

<Example 9>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 21 was used instead of Compound 5 in Example 1.

<Example 10>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 28 was used instead of Compound 5 in Example 1.

<Example 11>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 32 was used instead of Compound 5 in Example 1.

<Example 12>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 42 was used instead of Compound 5 in Example 1.

<Example 13>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 83 was used instead of Compound 5 in Example 1.

<Example 14>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 115 was used instead of Compound 5 in Example 1.

<Example 15>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 131 was used instead of Compound 5 in Example 1.

<Example 16>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 135 was used instead of Compound 5 in Example 1.

<Example 17>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 136 was used instead of Compound 5 in Example 1.

<Example 18>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 138 was used instead of Compound 5 in Example 1.

<Example 19>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 139 was used instead of Compound 5 in Example 1.

<Example 20>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 143 was used instead of Compound 5 in Example 1.

<Example 21>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 144 was used instead of Compound 5 in Example 1.

<Example 22>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 145 was used instead of Compound 5 in Example 1.

<Example 23>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 147 was used instead of Compound 5 in Example 1.

<Example 24>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 149 was used instead of Compound 5 in Example 1.

<Example 25>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 156 was used instead of Compound 5 in Example 1.

<Example 26>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 160 was used instead of Compound 5 in Example 1.

<Example 27>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 177 was used instead of Compound 5 in Example 1.

<Example 28>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 211 was used instead of Compound 5 in Example 1.

<Example 29>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 245 was used instead of Compound 5 in Example 1.

<Example 30>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 257 was used instead of Compound 5 in Example 1.

<Example 31>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 258 was used instead of Compound 5 in Example 1.

<Example 32>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 259 was used instead of Compound 5 in Example 1.

<Example 33>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 260 was used instead of Compound 5 in Example 1.

<Example 34>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 261 was used instead of Compound 5 in Example 1.

<Example 35>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 262 was used instead of Compound 5 in Example 1.

<Example 36>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 263 was used instead of Compound 5 in Example 1.

<Example 37>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 264 was used instead of Compound 5 in Example 1.

<Example 38>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 265 was used instead of Compound 5 in Example 1.

<Example 39>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 266 was used instead of Compound 5 in Example 1.

<Example 40>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 267 was used instead of Compound 5 in Example 1.

<Example 41>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 268 was used instead of Compound 5 in Example 1.

<Example 42>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 269 was used instead of Compound 5 in Example 1.

<Example 43>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 270 was used instead of Compound 5 in Example 1.

<Example 44>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 271 was used instead of Compound 5 in Example 1.

<Example 45>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 272 was used instead of Compound 5 in Example 1.

<Example 46>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 273 was used instead of Compound 5 in Example 1.

<Example 47>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 274 was used instead of Compound 5 in Example 1.

<Example 48>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 275 was used instead of Compound 5 in Example 1.

<Example 49>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 276 was used instead of Compound 5 in Example 1.

<Example 50>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 277 was used instead of Compound 5 in Example 1.

<Example 51>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 278 was used instead of Compound 5 in Example 1.

<Example 52>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 279 was used instead of Compound 5 in Example 1.

<Example 53>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 280 was used instead of Compound 5 in Example 1.

<Example 54>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 281 was used instead of Compound 5 in Example 1.

<Example 55>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 282 was used instead of Compound 5 in Example 1.

<Example 56>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 283 was used instead of Compound 5 in Example 1.

<Example 57>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 284 was used instead of Compound 5 in Example 1.

<Example 58>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 285 was used instead of Compound 5 in Example 1.

<Example 59>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 286 was used instead of Compound 5 in Example 1.

<Example 60>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 287 was used instead of Compound 5 in Example 1.

<Example 61>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 288 was used instead of Compound 5 in Example 1.

<Example 62>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 289 was used instead of Compound 5 in Example 1.

<Example 63>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 290 was used instead of Compound 5 in Example 1.

<Example 64>

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 291 was used instead of Compound 5 in Example 1.

<Comparative Example 1>

An organic light emitting device was manufactured in the same manner as in Example 1, except that RD having the following structure was used instead of Compound 5 in Example 1.

Experimental Example

The organic light emitting devices prepared in Examples 1 to 64 and Comparative Example 1, respectively, were connected to an external power source, and device characteristics were evaluated at room temperature using a current source and a photometer.

Specifically, the driving voltage, external quantum efficiency (EQE), lifetime characteristics (LT95), full width at half maximum and aspect ratio were measured with a current of 10 mA/cm ² , and the results are shown in Tables 1 and 2 below.

The aspect ratio is calculated as (the length of the long axis in the molecule centered on the metal (N-Metal-N direction)) / (the length of the short axis perpendicular to the long axis in the molecule centered on the metal), and the Gaussian molecular calculation program (Gaussian 16) It was measured by calculating the interatomic distance in the molecule through

LT95 lifetime is the time it takes for a display element to lose 5% of its initial brightness. LT95 is the most difficult customer specification to meet, and determines whether or not image burn-in occurs on the display.

Full Width at Half Maximum (FWHM) is also referred to as full width at half maximum, and means a wavelength width corresponding to 1/2 of the maximum value of a curve representing wavelengths (see FIGS. 3 and 4). A narrow half-width means that the purity of the color is high, which means that a drive-type device that expresses a desired color with a combination of light can be implemented with high efficiency and a high color reproduction rate can be obtained.

The full width at half maximum was evaluated through photoluminescence (PL) intensity measurement, and the Model/Maker of the measurement equipment was FS-5/Edinburgh Instruments.

dopant driving voltage
(%, relative value) EQE
(%, relative value) LT95
(%, relative value) half height
(%, relative value) aspect ratio
(%, relative value) Comparative Example 1 compound RD 100 100 100 100 100 Example 1 compound 5 97 109 115 75 130 Example 2 compound 7 99 103 101 77 134 Example 3 compound 8 98 115 109 72 121 Example 4 compound 10 97 127 128 72 104 Example 5 compound 11 97 133 135 70 104 Example 6 compound 15 96 139 109 80 130 Example 7 compound 16 96 145 103 83 120 Example 8 compound 19 97 145 154 67 154 Example 9 compound 21 97 145 179 67 154 Example 10 compound 28 98 152 160 65 154 Example 11 compound 32 96 115 141 78 124 Example 12 compound 42 96 121 122 72 104 Example 13 compound 83 97 152 147 65 154 Example 14 compound 115 97 145 145 65 154 Example 15 compound 131 95 133 154 58 116 Example 16 compound 135 97 127 128 60 135 Example 17 compound 136 96 139 141 58 113 Example 18 compound 138 95 142 167 55 102 Example 19 compound 139 95 145 173 55 101 Example 20 compound 143 94 164 141 63 115 Example 21 compound 144 94 170 128 67 108 Example 22 compound 145 94 152 179 50 106 Example 23 compound 147 95 170 186 48 135 Example 24 compound 149 95 170 212 48 135 Example 25 compound 156 96 176 192 48 135 Example 26 compound 160 94 139 173 62 106 Example 27 compound 177 94 145 171 50 107 Example 28 compound 211 96 167 174 47 135 Example 29 compound 245 96 164 203 47 139

dopant driving voltage
(%, relative value) EQE
(%, relative value) LT95
(%, relative value) half height
(%, relative value) aspect ratio
(%, relative value) Comparative Example 1 compound RD 100 100 100 100 100 Example 30 compound 257 94 174 188 48 135 Example 31 compound 258 95 180 192 48 135 Example 32 compound 259 96 182 194 46 135 Example 33 compound 260 94 175 190 49 128 Example 34 compound 261 95 181 193 47 135 Example 35 compound 262 95 183 195 47 140 Example 36 compound 263 95 185 196 47 140 Example 37 compound 264 96 187 198 46 128 Example 38 compound 265 93 168 165 49 108 Example 39 compound 266 95 172 175 49 130 Example 40 compound 267 93 166 160 49 110 Example 41 compound 268 95 181 220 48 135 Example 42 compound 269 95 182 225 48 135 Example 43 compound 270 95 183 240 48 135 Example 44 compound 271 95 183 230 48 135 Example 45 compound 272 95 179 194 47 125 Example 46 compound 273 96 181 177 48 132 Example 47 compound 274 96 178 168 49 133 Example 48 compound 275 95 178 188 48 135 Example 49 compound 276 95 183 195 46 135 Example 50 compound 277 94 188 160 56 146 Example 51 compound 278 94 190 165 55 146 Example 52 compound 279 94 190 163 55 135 Example 53 compound 280 94 192 168 54 135 Example 54 compound 281 93 195 145 60 140 Example 55 compound 282 93 197 150 59 140 Example 56 compound 283 95 175 180 48 137 Example 57 compound 284 95 177 182 48 137 Example 58 compound 285 96 179 184 47 131 Example 59 compound 286 96 177 195 47 135 Example 60 compound 287 96 179 190 47 129 Example 61 compound 288 96 174 187 47 129 Example 62 compound 289 96 173 188 48 133 Example 63 compound 290 93 171 186 58 135 Example 64 compound 291 93 172 181 59 133

RD, which is a dopant compound for the light emitting layer of Comparative Example 1 of the present invention, is different from the compounds of Examples of the present invention in that an additional fused ring is not formed in 2-phenylquinoline.

As can be seen from the results of Tables 1 and 2, the organic light emitting device to which the organometallic compound used in Examples 1 to 64 of the present invention is applied as a dopant in the light emitting layer has a lower driving voltage than Comparative Example 1, and an external Quantum efficiency (EQE) and lifetime (LT95) were improved, and the full width at half maximum was narrowed, resulting in improved color purity.

Although the embodiments of the present specification have been described in more detail with reference to the accompanying drawings, the present specification is not necessarily limited to these embodiments, and may be variously modified and implemented without departing from the technical spirit of the present specification. . Therefore, the embodiments disclosed in this specification are not intended to limit the technical spirit of the present specification, but to explain, and the scope of the technical spirit of the present specification is not limited by these embodiments. Therefore, it should be understood that the embodiments described above are illustrative in all respects and not restrictive. The protection scope of this specification should be construed according to the claims, and all technical ideas within the equivalent range should be construed as being included in the scope of this specification.

100, 4000: organic light emitting device
110, 4100: first electrode
120, 4200: second electrode
130, 230, 4300: organic layer
140: hole injection layer
150: hole transport layer
151: first hole transport layer
152: second hole transport layer
160: light emitting layer
161: first light emitting layer
162: second light emitting layer
170: electron transport layer
171: first electron transport layer
172: second electron transport layer
180: electron injection layer
191: N-type charge generation layer
192: P-type charge generation layer
240: first light emitting part (ST1)
250: first light emitting part (ST2)
260: charge generation layer
3000: organic light emitting display device
3010: substrate
3100: semiconductor layer
3200: gate insulating film
3300: gate electrode
3400: interlayer insulating film
3420, 3440: first and second semiconductor layer contact holes
3520: source electrode
3540: drain electrode
3600: color filter
3700: protective layer
3720: drain contact hole
3800: bank layer
3900: encapsulation film

Claims (10)

An organometallic compound represented by Formula I:

[Formula I]
In the above formula I,
M is a central coordination metal, molybdenum (Mo), tungsten (W), rhenium (Re), ruthenium (Ru), osmium (Os), rhodium (Rh), iridium (Ir), palladium (Pd), platinum (Pt) ) and one selected from the group consisting of gold (Au);
R is a fused ring formed by connecting X ₁ and X ₂ ;
R ₁ and R ₂ are each independently hydrogen, deuterium, halogen, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted A substituted C3-C20 cycloalkyl group, a substituted or unsubstituted C1-C20 heteroalkyl group, a substituted or unsubstituted C7-C20 arylalkyl group, a substituted or unsubstituted C1-C20 alkenyl group, a substituted or unsubstituted C3-C20 cycloalkenyl group, substituted or unsubstituted C1-C20 heteroalkenyl group, alkynyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 heteroaryl group, alkoxy one selected from the group consisting of an amino group, a silyl group, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a sulfanyl group, a sulfinyl group, a sulfonyl group, and a phosphino group;
Y is BR ₃ , CR ₃ R ₄ , C=O, CNR ₃ , SiR ₃ R ₄ , NR ₃ , PR ₃ , AsR ₃ , SbR ₃ , P(O)R ₃ , P(S)R ₃ , P( Se)R ₃ , As(O)R ₃ , As(S)R _{3 , As(Se)R 3 ,} Sb(O)R ₃ , Sb(S)R ₃ , Sb(Se)R ₃ , O, S , Se, Te, SO, SO ₂ , SeO, SeO ₂ , TeO and TeO ₂ One selected from the group consisting of;
R ₃ and R ₄ are each independently hydrogen, deuterium, halogen, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted A substituted C3-C20 cycloalkyl group, a substituted or unsubstituted C1-C20 heteroalkyl group, a substituted or unsubstituted C7-C20 arylalkyl group, a substituted or unsubstituted C1-C20 alkenyl group, a substituted or unsubstituted C3-C20 cycloalkenyl group, substituted or unsubstituted C1-C20 heteroalkenyl group, alkynyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 heteroaryl group, alkoxy one selected from the group consisting of an amino group, a silyl group, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a sulfanyl group, a sulfinyl group, a sulfonyl group, and a phosphino group;
X ₃ to X ₆ are each independently selected from CR ₅ and N;
Adjacent substituents of X ₃ to X ₆ may be fused to form a ring, and the ring may be a C5-C6 carbon ring or a heterocyclic ring;
X ₇ to X ₁₀ are each independently selected from CR ₆ and N;
R ₅ and R ₆ are each independently hydrogen, deuterium, halogen, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted A substituted C3-C20 cycloalkyl group, a substituted or unsubstituted C1-C20 heteroalkyl group, a substituted or unsubstituted C7-C20 arylalkyl group, a substituted or unsubstituted C1-C20 alkenyl group, a substituted or unsubstituted C3-C20 cycloalkenyl group, substituted or unsubstituted C1-C20 heteroalkenyl group, alkynyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 heteroaryl group, alkoxy one selected from the group consisting of an amino group, a silyl group, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a sulfanyl group, a sulfinyl group, a sulfonyl group, and a phosphino group;

is a bidentate ligand;
m is an integer of 1, 2 or 3, n is an integer of 0, 1 or 2, and m+n is an oxidation number of metal M.
According to claim 1,
The compound represented by Formula I is a compound represented by one structure selected from the group consisting of Formula II-1 and Formula II-2, an organometallic compound.

[Formula II-1]

[Formula II-2]
In Formula II-1 and Formula II-2,
Y, R ₁ to R ₂ , X ₃ to X ₁₀ ,

, m and n are the same as the definitions described in claim 1.
According to claim 1,
The compound represented by Formula I is a compound represented by a structure selected from the group consisting of Formula III-1 and Formula III-2, an organometallic compound.

[Formula III-1]

[Formula III-2]
In Formula III-1 and Formula III-2,
X ₁₁ to X ₁₄ are each independently selected from CR ₇ and N;
R ₇ are each independently hydrogen, deuterium, halogen, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C3 -C20 cycloalkyl group, substituted or unsubstituted C1-C20 heteroalkyl group, substituted or unsubstituted C7-C20 arylalkyl group, substituted or unsubstituted C1-C20 alkenyl group, substituted or unsubstituted C3-C20 Cyclic alkenyl group, substituted or unsubstituted C1-C20 heteroalkenyl group, alkynyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 heteroaryl group, alkoxy group, amino group , One selected from the group consisting of a silyl group, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a sulfanyl group, a sulfinyl group, a sulfonyl group, and a phosphino group;
Y, R ₁ to R ₂ , X ₅ to X ₁₀ ,

, m and n are the same as the definitions described in claim 1.
According to claim 1,
Wherein M is iridium (Ir), an organometallic compound.
According to claim 1,
The compound represented by Formula I is one selected from the group consisting of compounds 1 to 291 below, an organometallic compound.

.
According to claim 1,
The compound represented by Formula I is used as a red phosphorescent material or a green phosphorescent material, an organometallic compound.
a first electrode;
a second electrode facing the first electrode; and
An organic layer disposed between the first electrode and the second electrode,
The organic layer includes a light emitting layer,
The light emitting layer comprises an organometallic compound according to any one of claims 1 to 6, an organic electroluminescent device.
According to claim 7,
The organometallic compound is used as a dopant of the light emitting layer, an organic light emitting device.
According to claim 7,
The organic layer further comprises at least one selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, and an electron injection layer.
Board;
a driving element located on the substrate; and
An organic light emitting display device comprising: an organic light emitting device according to any one of claims 7 to 9 positioned on the substrate and connected to the driving device.

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